Anandamide
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| Anandamide | |
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| Chemical name | (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl) icosa-5,8,11,14-tetraenamide or arachidonoylethanolamide |
| Chemical formula | C22H37NO2 |
| Molecular mass | 347.53 g/mol |
| CAS number | 94421-68-8 |
| SMILES | CCCCC\C=C/C\C=C/C\C=C /C\C=C/CCCC(NCCO)=O |
| Missing image Anandamide_structure.png Chemical structure of anandamide | |
Anandamide, also known as arachidonoylethanolamine or AEA, is a naturally occurring endogenous cannabinoid neurotransmitter found in the brain of animals, as well as other organs. It was isolated, and its structure elucidated by William Devane and Lumir Hanus in the Laboratory of Raphael Mechoulam, at the Hebrew University in Jerusalem in 1992. It The name is taken from the Sanskrit word ananda, which means "bliss", and amide.
Anandamide's effects can be either central, in the brain, or peripheral, in other parts of the body.
The receptor that anandamide binds to is one member of the largest known family of receptors, the G protein-coupled receptors, which have a distinctive pattern in which the receptor molecule spans the cell membrane seven times over.
Anandamide receptors were originally discovered as being sensitive to Δ9-tetrahydrocannabinol (Δ9-THC), which is among the psychoactive cannabinoids found in marijuana. The discovery of anandamide came from research into the natural neurotransmitter that affected these receptors. Endogenous cannabinoids occur in minute quantities in cocoa (fermented Theobroma cacao beans), and in chocolate, though there is some controversy over whether they have any effects on the body in these quantities.
Anandamide receptors have been shown to be involved in the management of short term memory. Studies are under way to explore what role anandamide plays in human behavior, such as eating and sleep patterns, and the part it plays in pain relief.
Anandamide is also important for implantation of the early stage embryo in its blastocyst stadium into the uterus. Therefore cannabinoids like Δ9-THC might interfere with the earliest stages of human pregnancy.
See also
- Tetrahydrocannabinol (THC)
External links
Nature Medicine 10, 19 - 20 (2004) (http://dx.doi.org/10.1038/nm0104-19) THC: moderation during implantation
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